Upper East Side Confessional
by Quinton Michaels
Summary: Serena is in love, Blair is too, Nate can't stop sleeping with trash, and Chuck can't stop staring at Nate. Romances and friendships can only take so much right? This time the Upper East Siders are letting even more skeletons out of their closets.
1. Chapter 1

_Good Afternoon Upper East Siders, Gossip Girl here. We all know life at the top isn't always easy, so it's only natural us social kings and queens heavily indulge ourselves to ease our royal woes. The boys frequent pizza parlors where a dime bag is just as common as a slice of sausage and pepperoni and the girls max out their credit cards at places like Versace and Miu Miu. Your reputation is your biggest asset around here and no one knows that better than my Upper East Side Favorites.  
__**S**__ and __**B**__ were seen leaving Dior with several bags in tow. Buying dresses for __**C**__'s party perhaps?  
__**D**__ was spotted in Tiffany's of all places. Diamonds are a girl's best friend, but a gift like that seems a bit out of your price range if you ask me.  
__**N**__ and a mystery blonde (that strikes a strong resemblance to __**S**__, I might add) were headed up to his apartment.  
__**C**__'s finalizing plans a major blowout he's throwing this weekend. What's the occasion you ask? Like he needs one._

"Serena, he's not gay. Don't be ridiculous." Blair and Serena were sitting in a café during one of their many mid-afternoon shopping sprees.  
"B, all I'm saying is think about how many times you two have been alone together and he's never once tried to have sex with you." Serena set down her cup of espresso and licked her lips. The taste reminded her of kissing Dan.  
"Maybe he actually cares about my virtue. Unlike that sloppy Brooklynite you've been shacking up with." Serena rolled her eyes.  
"We're talking about Chuck Bass here, the most infamous playboy in all of Manhattan." Blair sighed heavily. She knew Serena was right, but she could not just give up on Chuck yet.  
"I have an idea! Get up, we're leaving."  
"B, wait!" Serena called out in vain. Blair was already out on the street hailing a cab. Serena tossed some money onto the table and ran out to catch up with her.

The elevator opened and Chuck stepped into his apartment. There was loud rock music playing from the stereo system, which slightly pissed him off. He couldn't get too angry though. The apartment didn't just belong to him. "Chuck, that you?" heard a voice call out over the music. Chuck turned the corner to discover Nate tangled up with some blonde on the couch.  
"Nathaniel. Sorry, I didn't mean to interrupt." Chuck muttered with a flat smile on his face.  
"What?" Nate yelled. Chuck walked over to the stereo and turned the volume down.  
"I said, I didn't mean to interrupt."  
"Don't worry about it. Natalie here was just leaving." Nate said locking eyes with girl in his lap.  
"Call me later, Natey?" The girl cooed lustily in Nate's ear.  
"Sure." Nate said as he tucked some if the girl's hair behind her ear. She slid out of Nate's grip and sauntered towards the elevator. Chuck waited until he heard the click of her heels disappear before he spoke.  
"Charming." Nate walked over to Chuck and slapped his shoulder.  
"Thanks for the compliment."  
"When are you going to stop fooling around with trash like that?" Nate shrugged as he flicked through their CD collection.  
"City girls are my type Chuck. I wouldn't even know how to handle the type of girls you fool around with."  
" Blair isn't your run of the mill city girl, Nathaniel." Nate laughed and set down the CDs he was looking at.  
"I'll just have to take your word for it. We never actually did it.  
"Wait, you never had sex with Blair?"  
"Nope. Now you're the proud owner of that particular V-card."  
" Yeah." Chuck laughed awkwardly.  
"Hey, I'm going to grab some pizza, wanna come?"  
"No, I have to some more things to take care of before Saturday." Nate was already putting on his coat.  
"Cool. I see you later then." Chuck watched Nate walk towards the elevator. His heart had been racing since he entered the apartment and his shoulder still tingled where Nate had touched him. He took a deep breath.  
"Why would Blair lie to me and what the hell is wrong with me?"

"This style is all the rage this season."  
"I don't know. I mean I want to look hot, but this is…"  
"Ridiculous." Serena finished Blair's sentence. They were currently in a lingerie boutique and Blair had just been squeezed into a tiny black, corset. "Blair you shouldn't have to wear something like that."  
"Serena! Don't you understand? This could decide the entire future of my relationship!" Serena's phone rang. "That better not be who I think it is!"  
"Hey Dan. No, I'm not doing anything." Blair shot Serena a nasty glance. "Sure. What time? Great. Okay, see you then."  
"Serena I swear if you ditch me to go hang out with that sorry excuse for a boyfriend…" Serena stood up and grabbed her coat  
"Sorry B, but Dan wants to meet me for coffee in an hour, and I have to get back to the apartment to pick out an outfit."  
"Take this thing off." Blair gestured towards the saleswoman. "Serena, wait, I'll come with you.  
" Okay." Serena said as she adjusted her hair in a nearby mirror. The saleswoman was struggling to get Blair out of the corset.  
"Never mind! I'll just take it!" Blair yelled as she dug in her purse for some money. She threw some bills at the woman. "Does this cover it?" The woman nodded, bewildered. "Blair slid her arms into her coat and gathered her bags.  
" Ready?" Serena said satisfied with her reflection.  
"Yes. Let's get out of here." Blair said as she headed towards the entrance. When they got outside, they ran into Nate who had just come out of a pizza parlor down the street.  
"Great. Look who it is."  
" Nice outfit. Are you and Chuck planning a special night?"  
" No! An even if we were it'd be none of your business, Nate." Blair spat back at him while adjusted her corset.  
"From what I hear it doesn't sound like you two need a special occasion." Blair's eyes widened.  
"Wait, was has Chuck told you?" Serena interjected.  
"Well, nothing in detail really, but he did make it clear he had taken Blair's you-know-what."  
"He certainly has not!" Blair shouted.  
"Wait if Chuck didn't then who…"  
"Blair maybe we should just go." Serena said as she tried to flag down a cab.  
"Oh God, how can this day get any worse!" A cab stopped next the trio.  
"Finally! Let's go B." As Serena grabbed Blair's arm, her corset popped open.  
"Whoa!" Nate marveled.  
"Can it Archibald!" Blair screamed as she snatched her coat shut and piled into the cab with Serena. Nate watched the cab pull away from the curb.  
"I should get pizza way more often."


	2. Chapter 2

"I don't even see why you're bothering to change." Blair was lounging on Serena's bed and flipping through a magazine. Serena came out of her closet wearing a leather miniskirt.  
"B, I've told already, I really like Dan."  
"Fine, but just because you're dating someone cheap doesn't mean you have to look the part."  
"So, I'm guessing that's a no-go on the leather then." Blair locked eyes with Serena.  
"Do you even have to ask?"  
"Blair, did you even give Dan a chance?" Serena came out of her closet again wearing nothing, but a bra and pair of jeans. "He's really nice and so smart." She sat on the bed and flopped backwards. Blair blushed slightly at Serena's half-naked body and stood up.  
"I simply don't see any point in me giving him a chance, but despite that I will decide what you're going to wear since you seem completely incapable of doing so." Blair strode into Serena's closet.  
"I promise, just spend a little time with him and you'll see." Blair's phone buzzed next to Serena. She sat up to answer it. "Uh-oh, B. Minion alert. Hi Penelope. Yes, she's right here. No, I don't think you can buy golf clubs at Burberry." Blair tossed a jacket on the bed and took her phone from Serena.  
"Wear that with your Gucci boots. What Penelope? How should I know? Just grab a bottle of cologne and call it a day. Yes! Bye. I swear am surrounded by a never-ending torrent of incompetence. It shouldnot be that hard to buy a present for an old man."  
" Oh, I forgot it was Cyrus's birthday on Sunday. Isn't your mom planning some huge brunch?" Serena said while slipping into her boots. Blair sighed heavily.  
"Yes. And of course I'm obliged to attend." Serena was at a mirror putting her hair into a ponytail.  
"I like your mom's brunches. The caterers she hires make the best mimosas. How do I look?" Blair walked over and stood behind Serena.  
"Ah yes, that will be the only redeeming factor about Sunday. See, S? You look fantastic and all thanks to me." Serena smiled at Blair's reflection and turned around to hug her.  
"What would I do without you, B?"

Chuck was in a limo headed back to his apartment when his phone rang. It was Nate. "Nathaniel, how are you?"  
"I think we need to talk." Chuck shifted uncomfortably in his seat. Nate sounded strange.  
"What about?"  
"I ran into Serena and Blair."  
"Okay."  
"Blair was wearing a corset under her coat and the both of them seemed in a rush to get home.  
" Not to be rude Nathaniel, but could you get to the point."  
" Blair said you didn't take her virginity." Chuck was absolutely silent. "I think something's going on between Serena and Blair." More silence. "Chuck you still there?"  
"Yeah. Nathaniel I need some time to process this. We'll talk more later.  
"Alright then. Take care, man." Chuck didn't know what to think or say. Was Nate mad that he lied about taking Blair's virginity? Could Blair and Serena honestly have something going on? He knew the one person that may have the answer to at least one of those questions.  
"Driver, I want to make a stop before heading home."

Serena stared into Dan's eyes. They were always so sure, content, as if he never needed anything. She hoped he needed her as much as she needed him. "What are thinking about?" she asked  
"You."  
"What about me?" Serena rubbed Dan's leg with hers. No matter how much she believed in this relationship, she was in the same predicament as Blair. He moved his leg away, which didn't serve to alleviate her fears.  
"About how much I love spending time with you," Did he just say he loved her? Serena needed to get a grip. "And how I don't mind hanging out with your friends anymore." Weird. It always seemed like Dan would do anything and everything to avoid hanging out with Serena's friends up until now.  
"Speaking of my friends, Chuck's throwing this party tomorrow night. Blair and her posse are going so I thought we'd stay in, just the two of us." Dan took a long sip out of his coffee mug.  
"You know, I actually wouldn't mind going." Serena just didn't get it. Would he really rather go to party where he hardly knew anyone than spend time alone with her?  
"I just thought since we haven't spent much time alone together…" Dan grabbed her hand in his and looked into her eyes.  
"I'll do wherever you want us to do Serena." Great, now she felt guilty.  
"You know what? Why stay in? Let's go out and have a good time." She tried to sound convincing. Dan smiled warmly and squeezed her hand.  
"Look, I'm sure we'll have a lot of fun."


End file.
